Synthesis, spectral characterization, chemical reactivity and anticancer behaviors of some novel hydrazone derivatives: Experimental and theoretical insights

• Published in: Journal of molecular structure Vol. 1253; p. 132224
• Main Authors: Çakmak, Reşit, Başaran, Eyüp, Kaya, Savaş, Erkan, Sultan
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 05.04.2022
• Subjects: Anticancer molecules; Chemical reactivity; DFT; Hydrazones; Molecular docking; Hydrazones; Anticancer molecules; DFT; Chemical reactivity; Molecular docking
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2021.132224

•Two novel hydrazone derivatives were designed and synthesized.•A detailed theoretical investigation about the chemical reactivities was presented.•Molecular docking calculations support the idea of which the molecules can exhibit anticancer performance.•Calculations made and experimental procedures in this paper will be useful for the synthesis of novel hydrazone derivatives in the future studies. In this research, two new hydrazone derivatives; namely compound 1 (N'-(4-((2-hydroxyethyl)(methyl)amino) benzylidene)nicotinohydrazide) and compound 2 (N'-(4-((2-hydroxyethyl)(methyl)amino) benzylidene)isonicotinohydrazide), were designed, successfully synthesized with high purity by treatment of N-methyl-N-(2-hydroxyethyl)-4-aminobenzaldehyde with nicotinic hydrazide and isoniazid, respectively. Spectroscopic characterization of the synthesized compounds was carried out by using FT-IR, UV–Vis, HRMS, 1H- and 13C- NMR spectroscopic techniques, and elemental analysis (C, H, N). For the synthesized compounds, important quantum chemical parameters like frontier orbital energies, hardness, softness, chemical potential, back-donation energy, first electrophilicity index, second electrophilicity index, electrodonating power, electroaccepting power were calculated and the relations with the chemical stability of these parameters were discussed as detailed. Additionally, anticancer properties of the mentioned compounds were analyzed with the help of Molecular Docking studies. [Display omitted]